5-Aminobenzimidazole → HCID 66712833, compound

HRID 1262367Notes

Reaction equation

HRID 1262367 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:6]2[N:5]=1)=O.[N:23]1[C:27]2[CH:28]=[CH:29][C:30]([NH2:32])=[CH:31][C:26]=2[NH:25][CH:24]=1>>[N:23]1[C:27]2[CH:28]=[CH:29][C:30]([NH:32][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=5)[N:6]4[N:5]=3)=[CH:31][C:26]=2[NH:25][CH:24]=1

Participants

3

Reactant 2

HCID 136235-AminobenzimidazoleHCID 667110462-(Methylsulfinyl)-7-(4-(methylsulfonyl)phenyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66712833HCID 66712833, compound

Procedure

Following the synthetic and purification procedures described in Example 1293d, 2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (75 mg, 0.22 mmol) was coupled with 3H-benzimidazol-5-ylamine (51 mg, 0.38 mmol) at 105° C. in a for 86 h to afford the title compound. Yield of TFA salt: 46 mg (40%) of brown powder; LC/MS: 405 (M+H); HPLC: 90% pure, RT=2.14 min; 1H NMR: (DMSO, δ) 9.96 (s, 1H), 9.48 (s, 1H), 9.13 (s, 1H), 8.51 (d, J=8.6, 2H), 8.18 (s, 1H), 8.07 (d, J=8.6, 2H), 7.86 (m, 2H), 7.42 (d, J=4.8, 1H), 7.07 (d, J=4.8, 1H), 3.28 (s, 3H)-benzimidazole NH presumably underwent rapid exchange with residual water.

Workup

  1. custompurification procedures
  2. customfor 86 h

Sources & evidence

ORD record
ord-45680d145ad54410a46e5b470eab1327
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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